Journal - Harrowing Journeys
A reflection on choosing the difficult road - from the journal
The path to the life I want has never been paved and gentle.
It has been rutted and rotten, winding and steep.
Whenever it begins to feel easy, around the next bend, I come to a peaty quagmire of mud and blood.
The thing is, though, I am filled with gratitude for this.
“Here’s to the peaty quagmires of mud and blood that leave us wondering if we’ve taken a wrong turn.“
I became aware, many years ago, that the more difficult the journey I face, the greater the reward of the destination.
Every single time.
There is a peculiar promise that we make to ourselves when we’re young. We convince ourselves that life is difficult because we’re inexperienced. We tell ourselves that if we work hard enough, endure enough hardship, and make enough wise decisions, one day the road will level out. The difficult years will be behind us. The storms will become less frequent. We will finally arrive.
For much of my life, I believed that.
When I looked at people a generation older than me, I imagined they had somehow earned an easier existence. They had already fought the battles that lay ahead of me. Surely there came a point where the climbing stopped and a man was allowed to walk on level ground for a while.
It has taken me nearly sixty years to realize that no such place exists.
Life has a habit of waiting until you’re comfortable before revealing another bend in the trail. Beyond it there is usually another climb, another uncertainty, another season that demands more of you than the one before. It doesn’t seem to matter whether the challenge arrives through work, relationships, health, or simple circumstance. The landscape changes, but the journey never really becomes easier.
For a long time I mistook those difficult stretches for interruptions. I thought they were standing between me and the life I wanted to live. If only I could get through this problem, I would finally arrive at the chapter where life could simply be enjoyed.
Looking back now, I can see that I misunderstood almost everything.
The difficult stretches were never standing in the way.
They were the way.
When I think back over my own life, I don’t remember the comfortable years with much clarity. They blur together in a way that surprises me. It is the demanding seasons that remain vivid. Long days guiding in the North. Building a business with more optimism than experience. Watching that chapter close. Learning that health is never guaranteed. Beginning again when I thought I had already earned the right not to.
Most recently, it has been this strange and wonderful decision to step aboard an old wooden sailboat and build a quieter life on a small island at the edge of the Pacific. On paper, it makes very little sense. It is slower, less convenient, and certainly less predictable than the life I left behind.
And yet I cannot remember a time when I have felt more alive.
That realization has forced me to ask an uncomfortable question.
If the most meaningful chapters of my life have always demanded sacrifice, uncertainty, and perseverance, why have I spent so much of my life wishing those things away?
Perhaps comfort isn’t the prize I imagined it to be.
Perhaps the satisfaction we seek doesn’t come from avoiding hardship at all. Perhaps it comes from discovering that we are capable of more than we believed. Every worthwhile pursuit I’ve known has required patience before reward. A clean cast into a difficult current. A long stalk with a bow. Learning the tides well enough to gather a meal from the shoreline. Restoring an old boat. Building a marriage. None of these things can be hurried, and none of them are made richer by becoming easier.
They are valuable precisely because they ask something of us.
That is not to romanticize suffering. There are seasons I would never wish to repeat, and losses I would gladly have avoided. But I can no longer say that I wish for an easier road. An easier road would almost certainly have led somewhere else.
It would not have led me here.
These days, when I feel the ground becoming soft beneath my boots once again, I try to greet it differently. I remind myself that every meaningful chapter of my life has begun with uncertainty. Every worthwhile destination has first required me to cross a patch of difficult country.
I still don’t enjoy the mud.
I still question the climb.
But I’ve stopped questioning whether the journey is worth it.
It always has been.
So here’s to the rutted roads. The rotten bridges. The steep climbs and the uncertain weather. Here’s to the peaty quagmires of mud and blood that leave us wondering if we’ve taken a wrong turn.
And here’s to discovering, somewhere beyond the next bend, that we hadn’t lost the path at all.
We had simply found the one that was always meant to be ours.
Here’s to harrowing journeys.







A lesson & truth I believe we all learn one day.
To harrowing journeys.
Stoked for you and your island life adventure.